An automated metadata discovery, assignment, and submission system is disclosed. The system includes a photosharing service coupled to a network through a server, where the server stores metadata fields. The system also includes at least one client computer capable of communicating with the server over the network, where the client computer stores a plurality digital files and an automation application. When executed, the automation application establishes communication with the photosharing service and downloads the metadata fields. The content of a first file is then automatically analyzed and one or metadata values are assigned to the downloaded metadata fields based on the analysis. In addition, the automation application automatically discovers any pre-existing metadata values associated with the file and uses the metadata values to populate corresponding downloaded metadata fields. Both the pre-existing and automatically assigned metadata values are then displayed to the user for viewing and editing. The metadata values assigned to the file are recoded for use with a next image, and the file and the metadata values are uploaded to the photosharing service for storage.